Sodium Hydroxide → 6-Trityloxyhexanoic acid

HRID 467390Notes

Reaction equation

HRID 467390 reaction equation
[OH-].[Na+].[C:3]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.O>[C:3]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67198977Methyl 6-trityloxy-hexanoate

Product 1

HCID 671997996-Trityloxyhexanoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of 5 M NaOH (17.5 mL, 87.5 mmol) was added to a stirring solution of 15a (20.1 g, 51.6 mmol) in 130 mL of THF and 52.5 mL of water at room temperature. After stirring for 2 days, 3.1 mL of 5 M NaOH (15.5 mmol) was added, and stirring was continued for another 2 days. The THF was removed under reduced pressure, then the aqueous residue was acidified with 1 M HCl to pH 5 and extracted with diethyl ether. The combined organic layers were washed with brine and dried over MgSO4. The diethyl ether was removed under reduced pressure, and the resulting crude powder was recrystalized in hexanes to yield 15.1 g (78%) of white powder 16a. Mp 114-116° C. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.22 (3H, m, o-Ar), 3.05 (2H, t, 3JH—H=6.4 Hz, HO—CH2), 2.33 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.56-1.68 (4H, m, 2CH2), 1.36-1.47 (2H, m, CH2). 13C-NMR (100 MHz, CDCl3, δH ppm): 180.26, 144.36, 128.62, 127.66, 126.79, 86.30, 63.24, 33.98, 29.63, 25.74, 24.48. HRMS (EI): m/z calcd 374.1882 (C25H26O3), found 374.1883 [M]+.

Workup

  1. stirringstirring
  2. waitwas continued for another 2 days
  3. customThe THF was removed under reduced pressure
  4. extractionextracted with diethyl ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customThe diethyl ether was removed under reduced pressure
  8. customthe resulting crude powder was recrystalized in hexanes

Sources & evidence

ORD record
ord-ce13eab8b62b4c3c8e856f110a9af84a
Source dataset
uspto-grants-2014_01
Patent number
US08623326B2

Reaction notes

Loading…